WO2021101220A1 - Composé hétérocyclique, dispositif électroluminescent organique le comprenant, composition pour couche organique de dispositif électroluminescent organique, et procédé de fabrication de dispositif électroluminescent organique - Google Patents

Composé hétérocyclique, dispositif électroluminescent organique le comprenant, composition pour couche organique de dispositif électroluminescent organique, et procédé de fabrication de dispositif électroluminescent organique Download PDF

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WO2021101220A1
WO2021101220A1 PCT/KR2020/016200 KR2020016200W WO2021101220A1 WO 2021101220 A1 WO2021101220 A1 WO 2021101220A1 KR 2020016200 W KR2020016200 W KR 2020016200W WO 2021101220 A1 WO2021101220 A1 WO 2021101220A1
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emitting device
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이영진
모준태
김동준
오한국
변지윤
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엘티소재주식회사
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Priority to JP2021571737A priority Critical patent/JP2023500759A/ja
Priority to CN202080048175.3A priority patent/CN114096535A/zh
Priority to US17/612,956 priority patent/US20220259187A1/en
Priority to EP20889890.8A priority patent/EP4063359A4/fr
Publication of WO2021101220A1 publication Critical patent/WO2021101220A1/fr

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Definitions

  • the present specification relates to a heterocyclic compound, an organic light-emitting device including the same, a composition for an organic material layer of the organic light-emitting device, and a method of manufacturing an organic light-emitting device.
  • An organic electroluminescent device is a kind of self-emission type display device, and has advantages in that it has a wide viewing angle, excellent contrast, and a fast response speed.
  • the organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then emit light while disappearing.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as needed.
  • a compound capable of constituting an emission layer by itself may be used, or a compound capable of serving as a host or a dopant of the host-dopant-based emission layer may be used.
  • a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.
  • materials usable in an organic light-emitting device such as an appropriate energy level, electrochemical stability, and thermal stability, and can play various roles required in an organic light-emitting device depending on the substituent
  • Patent Document 1 U.S. Patent No. 4,356,429
  • the present application relates to a heterocyclic compound, an organic light-emitting device including the same, a composition for an organic material layer of the organic light-emitting device, and a method of manufacturing an organic light-emitting device.
  • a heterocyclic compound represented by the following Formula 1 is provided.
  • N-Het is a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocyclic group containing one or more N,
  • L is a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group, a is an integer of 1 to 3, and when a is 2 or more, L is the same as or different from each other,
  • A is a substituted or unsubstituted C6 to C60 aryl ring; Or a substituted or unsubstituted C2 to C60 heteroaryl ring,
  • Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 Forms a heterocycle, d is an integer of 0 to 2, when d is 2, two Ra are the same as or different from each other,
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted silyl group; And selected from the group consisting of a substituted or unsubstituted
  • the first electrode A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes at least one heterocyclic compound represented by Formula 1 It provides a light emitting device.
  • a composition for an organic material layer of an organic light emitting device including a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 is provided.
  • Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • R51 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; A substituted or unsubstituted phosphine oxide group; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or two or more groups adjacent to each
  • the compound described in the present specification can be used as an organic material layer material of an organic light emitting device.
  • the compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in the organic light emitting device.
  • the compound can be used as a material for the light emitting layer of the organic light emitting device.
  • the compound may be used alone as a light-emitting material, and two compounds may be used together as a light-emitting material, and may be used as a host material for a light-emitting layer.
  • the compound of Formula 1 since the compound of Formula 1 has an O atom with a high electronegativity in the center of the core structure, it has excellent electron transfer capability and has suitable characteristics in exciton blocking.
  • the carbazole structure condensed on one benzene ring of the dibenzofuran structure is substituted at positions 1 and 3, the HOMO orbital and LUMO orbital due to steric can be separated and electron transfer is facilitated.
  • 1 to 3 are diagrams each schematically showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application.
  • PL 5 is a photoluminescence (PL) measurement data of only a first host and a second host according to Example 71 of the present application.
  • PL photoluminescence
  • "when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that can come as a substituent are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope, and in this case, the content of deuterium may be 0% to 100%.
  • deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as a nucleus, and hydrogen- It can be expressed as 2, and the element symbol can also be written as D or 2H.
  • an isotope meaning an atom having the same atomic number (Z) but different mass number (A) has the same number of protons, but neutrons
  • the number of (neutron) can be interpreted as other elements.
  • the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula), it will be expressed as 20%.
  • T1 in the formula the total number of substituents that the phenyl group can have
  • T2 in the formula the number of deuterium is 1
  • I can. That is, 20% of the deuterium content in the phenyl group can be represented by the following structural formula.
  • the "phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.
  • the halogen may be fluorine, chlorine, bromine or iodine.
  • the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20.
  • Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group,
  • the alkenyl group includes a linear or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.
  • Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(Naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the alkynyl group includes a linear or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.
  • the alkoxy group may be a straight chain, branched chain, or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20 carbon atoms.
  • the cycloalkyl group includes monocyclic or polycyclic having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group.
  • the other cyclic group may be a cycloalkyl group, but may be a different type of cyclic group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like.
  • the number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20.
  • the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes monocyclic or polycyclic having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic means a group in which a heterocycloalkyl group is directly connected or condensed with another ring group.
  • the other cyclic group may be a heterocycloalkyl group, but may be a different type of cyclic group, such as a cycloalkyl group, an aryl group, a heteroaryl group, and the like.
  • the number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.
  • the aryl group includes monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic refers to a group in which an aryl group is directly connected or condensed with another ring group.
  • the other cyclic group may be an aryl group, but may be another type of cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like.
  • the aryl group includes a spiro group.
  • the number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25.
  • aryl group examples include phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyre Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof And the like, but are not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • fluorenyl group when substituted, it may have the following structure, but is not limited thereto.
  • the heteroaryl group includes S, O, Se, N, or Si as a hetero atom, includes a monocyclic or polycyclic having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic means a group in which a heteroaryl group is directly connected or condensed with another ring group.
  • the other cyclic group may be a heteroaryl group, but may be another type of cyclic group such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like.
  • the number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.
  • heteroaryl group examples include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl Group, isothiazolyl group, triazolyl group, furazinyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , Thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozoliryl group, naphthyridyl group,
  • the amine group is a monoalkylamine group; Monoarylamine group; Monoheteroarylamine group; -NH 2 ; Dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; And it may be selected from the group consisting of an arylheteroarylamine group, the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluore
  • nilamine group phenyltriphenylenylamine group, biphenyltriphenylenylamine group, and the like, but are not limited thereto.
  • an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
  • the heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.
  • the phosphine oxide group includes a diphenylphosphine oxide group and a dinaphthylphosphine oxide, but is not limited thereto.
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR104R105R106, R104 to R106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. It is not limited.
  • the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.
  • I can.
  • two substituents substituted with an ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.
  • substitution means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, When two or more are substituted, two or more substituents may be the same or different from each other.
  • R, R'and R are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R, R'and R are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C40 alkyl group; A substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.
  • R, R'and R” are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C40 alkyl group; Or a substituted or unsubstituted C6 to C40 aryl group.
  • R, R'and R” are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted C6 to C20 aryl group.
  • R, R'and R” are the same as or different from each other, and each independently a C1 to C20 alkyl group; Or a C6 to C20 aryl group.
  • R, R'and R” are the same as or different from each other, and each independently a C1 to C10 alkyl group; Or a C6 to C10 aryl group.
  • R, R'and R” are the same as or different from each other, and each independently a linear C1 to C10 alkyl group; Or a monocyclic C6 to C10 aryl group.
  • R, R'and R” are the same as or different from each other, and each independently a methyl group; Or a phenyl group.
  • a heterocyclic compound represented by Formula 1 is provided.
  • Formula 1 may be represented by one of the following Formulas 3 to 6.
  • N-Het, L, A, Ra, R1 to R6, a, b, c, and d are the same as those in Formula 1.
  • R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 Form a heterocycle,
  • R15 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • Rb is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C60 aryl group, m is an integer of 0 to 4, and when m is 2 or more, Rb is the same as or different from each other.
  • R12 and R13 when R12 and R13 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, the formula At least one of R11, R14, R15 to R18 and Rb of 1-1 and Formula 1-3 is deuterium; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And it may be selected from the group consisting of a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R11 in Formulas 1-1 and 1-3 of the present application when R12 and R13 are bonded to each other to form an unsubstituted C6 to C40 aromatic hydrocarbon ring, R11 in Formulas 1-1 and 1-3 , At least one of R14, R15 to R18 and Rb is deuterium; A substituted or unsubstituted C6 to C60 aryl group; And it may be selected from the group consisting of a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R11, R14, and R15 in Formulas 1-1 and 1-3 At least one of R18 and Rb is deuterium; Phenyl group; Biphenyl group; And it may be selected from the group consisting of a naphthyl group.
  • R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or R11 and R12; Or R13 and R14 may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.
  • R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or R11 and R12; Alternatively, R13 and R14 may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.
  • R11 to R14 are each independently hydrogen; heavy hydrogen; Phenyl group; Or R11 and R12 selected from the group consisting of a biphenyl group and a naphthyl group; Alternatively, R13 and R14 may be bonded to each other to form a benzene ring.
  • N-Het is a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocycle containing one or more N.
  • N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of C6 to C60 aryl groups and C2 to C60 heteroaryl groups, and C2 to C2 containing at least one N It is a C60 monocyclic or polycyclic heterocycle.
  • N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of C6 to C40 aryl group and C2 to C40 heteroaryl group, and C2 to C2 containing at least one N It is a C40 monocyclic or polycyclic heterocycle.
  • N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of C6 to C30 aryl groups and C2 to C30 heteroaryl groups, and C2 to C2 containing at least one N It is a C30 monocyclic or polycyclic heterocycle.
  • N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a dimethylfluorenyl group. It is a C2 to C30 monocyclic or polycyclic heterocycle containing one or more N.
  • N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a dimethylfluorenyl group.
  • It is a C2 to C30 monocyclic or polycyclic heterocycle containing 1 or more and 3 or less N.
  • N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a dimethylfluorenyl group. It may be a triazine group.
  • N-Het is substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a dimethylfluorenyl group.
  • Triazine group A pyrimidine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group and a naphthyl group; A quinazoline group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group; A quinoline group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group; A quinoxaline group unsubstituted or substituted with a phenyl group or a naphnyl group; Benzofuro[3,2-d]pyrimidine group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group; Benzofuro[2,3-d]pyrimidine group unsubstituted or substituted with a phenyl group, a biphen
  • the benzofuro[3,2-d]pyrimidine group may have the following structure.
  • the benzofuro[2,3-d]pyrimidine group may have the following structure.
  • the benzo[4,5]thieno[3,2-d]pyrimidine group may have the following structure.
  • the benzo[4,5]thieno[2,3-d]pyrimidine group may have the following structure.
  • the N-Het is a C6 to C20 aryl group; Or deuterium; may be further substituted.
  • the N-Het is deuterium; Phenyl group; Or it may be further substituted with a naphthyl group.
  • the N-Het may be represented by Formula 2-1 below.
  • X1 is N or CR21
  • X3 is N or CR23
  • X5 is N or CR25
  • At least one of X1, X3 and X5 is N,
  • R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Formula 2-1 may be selected from the following structural formulas.
  • R21 to R25 are the same as those in Formula 2-1.
  • L is a direct bond; A substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.
  • L is a direct bond; A substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.
  • L is a direct bond; C6 to C40 arylene group; Or it may be a C2 to C40 heteroarylene group.
  • L is a direct bond; C6 to C40 monocyclic arylene group; Or it may be a C2 to C40 monocyclic heteroarylene group.
  • L is a direct bond; Or it may be a phenylene group.
  • L may be a direct bond
  • L may be a phenylene group.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to When forming a C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, N-Het of Formula 1 is substituted or unsubstituted, and a C2 to C60 monocyclic ring containing 1 or more and 2 or less N Or it may be a polycyclic heterocycle.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • N-Het of Formula 1 is substituted or unsubstituted, and C2 to C40 monocyclic or It may be a polycyclic heterocycle.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • N-Het of Formula 1 is substituted or unsubstituted, and C2 to C20 monocyclic or It may be a polycyclic heterocycle.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • N-Het of Formula 1 is substituted or unsubstituted with a C6 to C20 aryl group, and contains 1 or more and 2 or less N It may be a C2 to C20 monocyclic or polycyclic heterocycle.
  • N-Het of Formula 1 is a pyrimidine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group and a naphthyl group; A quinazoline group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group; A quinoline group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group; A quinoxaline group unsubstituted or substituted with a phenyl group or a naphnyl group;
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to
  • the deuterium content of Formula 1 may be 10% or more and 100% or less.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • the deuterium content of Formula 1 may be 15% or more and 90% or less.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • the deuterium content of Formula 1 may be 20% or more and 80% or less.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • the deuterium content of Formula 1 may be 20% or more and 40% or less.
  • the deuterium content of Formula 1 may mean a ratio in which deuterium is substituted among positions that may come with the substituents of Formula 1. That is, if the total number of positions at which the substituents can be substituted in Chemical Formula 1 are 40, and 20 of them are substituted with deuterium, the deuterium content of Chemical Formula 1 may be expressed as 50%.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to
  • L in Formula 1 is a substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • L in Formula 1 is a substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • L in Formula 1 is a substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C2 to C20 heteroarylene group.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • L in Formula 1 is a C6 to C20 arylene group; Or it may be a C2 to C20 heteroarylene group.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • L in Formula 1 may be a C6 to C20 arylene group.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to C60
  • L in Formula 1 may be a phenylene group.
  • R11 to R15, R18, and Rb of Formula 1-2 are all hydrogen, or two adjacent groups of R11 to R14 of Formula 1-2 are bonded to each other to unsubstituted C6 to
  • N-Het of Formula 1 is substituted or unsubstituted
  • a polycyclic heterocycle, or the deuterium content of Formula 1 is 10% or more and 100% or less
  • L in Formula 1 is a substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.
  • A is a substituted or unsubstituted C6 to C60 aryl ring; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl ring.
  • A is a substituted or unsubstituted C6 to C40 aryl ring; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl ring.
  • A may be a substituted or unsubstituted C6 to C40 aryl ring.
  • A may be a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthyl ring.
  • A may be a benzene ring unsubstituted or substituted with a C6 to C30 aryl group or a naphthyl ring unsubstituted or substituted with a C6 to C30 aryl group.
  • A may be a benzene ring or a naphthyl ring unsubstituted or substituted with a phenyl group.
  • A may be further substituted with deuterium.
  • Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 It can form a heterocycle.
  • Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C40 aryl group; And a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 It can form a heterocycle.
  • Ra is hydrogen; heavy hydrogen; And a C6 to C40 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a C6 to C40 aromatic hydrocarbon ring.
  • Ra is hydrogen; heavy hydrogen; And C6 to C40 monocyclic or polycyclic aryl groups, or two or more groups adjacent to each other may be bonded to each other to form a C6 to C40 monocyclic or polycyclic aromatic hydrocarbon ring.
  • Ra is hydrogen; heavy hydrogen; And selected from the group consisting of a phenyl group, or two or more groups adjacent to each other may be bonded to each other to form a benzene ring.
  • R1 to R4 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted silyl group; And selected from the group consisting of a substituted or unsubstituted amine
  • R1 to R4 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 It can form a heterocycle.
  • R1 to R4 are each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted C6 to C40 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.
  • R1 to R4 are each independently hydrogen; heavy hydrogen; And a monocyclic or polycyclic C6 to C40 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a monocyclic or polycyclic C6 to C60 aromatic hydrocarbon ring.
  • R1 to R4 are each independently hydrogen; heavy hydrogen; And a monocyclic or polycyclic C6 to C20 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a monocyclic or polycyclic C6 to C30 aromatic hydrocarbon ring.
  • R1 to R4 are each independently hydrogen; heavy hydrogen; Phenyl group; It is selected from the group consisting of a biphenyl group and a naphthyl group, or two or more groups adjacent to each other may be bonded to each other to form a benzene ring.
  • R5 and R6 may be hydrogen.
  • R5 and R6 may be deuterium.
  • R5 and R6 are hydrogen; Or deuterium.
  • both R5 and R6 may be hydrogen.
  • both R5 and R6 may be deuterium.
  • the heterocyclic compound of Formula 1 may be further substituted with deuterium.
  • the heterocyclic compound of Formula 1 may be substituted with deuterium by 10% or more and 100% or less.
  • R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 It can form a heterocycle.
  • R11 to R14 are each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted C6 to C40 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.
  • R11 to R14 are each independently hydrogen; heavy hydrogen; And a monocyclic or polycyclic C6 to C40 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a monocyclic or polycyclic C6 to C60 aromatic hydrocarbon ring.
  • R11 to R14 are each independently hydrogen; heavy hydrogen; And a monocyclic or polycyclic C6 to C20 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a monocyclic or polycyclic C6 to C30 aromatic hydrocarbon ring.
  • R11 to R14 are each independently hydrogen; heavy hydrogen; Phenyl group; It is selected from the group consisting of a biphenyl group and a naphthyl group, or two or more groups adjacent to each other may be bonded to each other to form a benzene ring.
  • R15 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R15 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R15 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.
  • R15 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C6 to C40 aryl group; Or it may be a C2 to C40 heteroaryl group.
  • R15 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a monocyclic or polycyclic C6 to C40 aryl group.
  • R15 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a phenyl group.
  • Rb is hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted C6 to C60 aryl group.
  • Rb is hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted C6 to C40 aryl group.
  • Rb is hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted C6 to C20 aryl group.
  • Rb is hydrogen; heavy hydrogen; Or it may be a C6 to C20 aryl group.
  • Rb is hydrogen; heavy hydrogen; Or it may be a C6 to C20 monocyclic or polycyclic aryl group.
  • Rb is hydrogen; heavy hydrogen; Or it may be a phenyl group.
  • R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C6 to C60 aryl group unsubstituted or substituted with deuterium, a C1 to C60 alkyl group or a C6 to C60 aryl group; Or it may be a C2 to C60 heteroaryl group.
  • R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C6 to C40 aryl group unsubstituted or substituted with deuterium, a C1 to C10 alkyl group or a C6 to C20 aryl group; Or it may be a C2 to C40 heteroaryl group.
  • R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a deuterium or naphthyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Dibenzofuran group; Dibenzothiophene group; Or it may be a dimethylfluorenyl group.
  • X1, X3, and X5 may be N.
  • At least two of X1, X3, and X5 may be N.
  • Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
  • a compound having the inherent characteristics of the introduced substituent can be synthesized.
  • a hole injection layer material, a hole transport material, a light emitting layer material, an electron transport layer material, and a substituent mainly used in the charge generation layer material used in manufacturing an organic light emitting device are introduced into the core structure to meet the conditions required by each organic material layer. It is possible to synthesize a material that makes it possible.
  • the energy band gap can be finely adjusted, while the properties at the interface between organic substances can be improved, and the use of the material can be varied.
  • the first electrode A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes at least one heterocyclic compound according to Formula 1
  • the device is provided.
  • the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes one heterocyclic compound according to Formula 1 above. Provides.
  • the first electrode A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes two heterocyclic compounds according to Formula 1
  • the device is provided.
  • the types of the heterocyclic compounds may be the same or different.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the organic light-emitting device may be a blue organic light-emitting device
  • the heterocyclic compound according to Formula 1 may be used as a material of the blue organic light-emitting device.
  • the heterocyclic compound according to Formula 1 may be included in the host material of the blue emission layer of the blue organic light emitting device.
  • the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material of the green organic light-emitting device.
  • the heterocyclic compound according to Formula 1 may be included in the host material of the green emission layer of the green organic light emitting device.
  • the organic light-emitting device may be a red organic light-emitting device
  • the heterocyclic compound according to Formula 1 may be used as a material of the red organic light-emitting device.
  • the heterocyclic compound according to Formula 1 may be included in the host material of the red emission layer of the red organic light emitting device.
  • the organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed using the above-described heterocyclic compound.
  • the heterocyclic compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.
  • the organic material layer may include an emission layer, and the emission layer may include the heterocyclic compound.
  • the organic material layer may include an emission layer, the emission layer may include a host material, and the host material may include the heterocyclic compound.
  • the organic material layer including the heterocyclic compound includes the heterocyclic compound represented by Formula 1 as a host, and may be used together with an iridium-based dopant.
  • the organic material layer may include an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer may include the heterocyclic compound.
  • the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.
  • the organic light emitting device of the present invention is a light emitting layer, a hole injection layer, a hole transport layer. It may further include one or two or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.
  • FIG. 1 to 3 illustrate a stacking sequence of an electrode and an organic material layer of an organic light-emitting device according to an exemplary embodiment of the present application.
  • the scope of the present application be limited by these drawings, and the structure of an organic light-emitting device known in the art may be applied to the present application.
  • an organic light-emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown.
  • an organic light-emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
  • the organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306.
  • a hole injection layer 301 a hole transport layer 302
  • a light emitting layer 303 a hole transport layer 302
  • a hole blocking layer 304 a hole blocking layer 304
  • an electron transport layer 305 an electron injection layer 306.
  • the scope of the present application is not limited by such a lamination structure, and other layers other than the light emitting layer may be omitted, or other necessary functional layers may be further added if necessary.
  • the organic material layer including the compound of Formula 1 may further include other materials as necessary.
  • the organic material layer may further include a heterocyclic compound represented by Formula 2 below.
  • Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • R51 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; A substituted or unsubstituted phosphine oxide group; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or two or more groups adjacent to each
  • the exciplex phenomenon refers to the formation of a dicomplex in an excited state through electron exchange between molecules having strong donor properties and molecules having strong acceptor properties.
  • FIG. 4 is a diagram illustrating an exciplex phenomenon. As shown in FIG. 4, when an exciplex phenomenon occurs, a new S1 energy level and a T1 energy level are formed, and a change in PL red-shifted from each molecule can be confirmed.
  • an exciplex which is a bicomplex form of an excited state between the donor and acceptor molecules, it has a new energy level different from that of the donor and acceptor, and the light emitted at this energy level is the donor. Red-shifted light is emitted than the light emitted by each of the and accepters, and the PL is measured to confirm this. Accordingly, from the PL data, it is possible to determine whether exciplex has occurred in this molecule by comparing the emission wavelength of a single host with that of a mixed host.
  • RISC Reverse Intersysterm Crossing
  • the red-shifted PL change is shown by injecting donor (p-Host), a heterocyclic compound of Formula 2, which is a bipolar compound, but does not have a strong acceptor ability as a bipolar compound. It is possible to form an exciplex, thereby helping to improve light-emitting characteristics.
  • donor (p-host)) corresponding to Formula 2 of the present invention having a good hole transport ability is injected, the lifespan can be significantly improved by appropriate movement of the light emitting zone in the light emitting layer.
  • Formula 2 may be represented by any one of Formulas 10 to 12 below.
  • R61 to R70 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And it is selected from the group consisting of a substituted or unsubstituted C2 to C60 heteroaryl group,
  • R71 to R74 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 Form a heterocycle,
  • Ar2 and Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • A1 is O; S; NAr4; Or CRdRe,
  • Rd and Re are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; Or a substituted or unsubstituted C6 to C60 aryl group,
  • Ar4 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • h and i are integers from 0 to 3
  • j is an integer from 0 to 2.
  • Chemical Formula 10 may be represented by Chemical Formula 10-1 or 10-2 below.
  • Formula 11 may be represented by Formula 11-1 or 11-2 below.
  • Chemical Formula 12 may be represented by any one of Chemical Formulas 12-1 to 12-4 below.
  • R81 and R82 are the same as or different from each other, and each independently a substituted or unsubstituted C10 or more aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • R83 is a substituted or unsubstituted C10 or less aryl group.
  • Ar2 to Ar4 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Ar2 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C40 alkyl group; A substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.
  • Ar2 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group, a C1 to C20 alkyl group, a C6 to C40 aryl group, and a C2 to C40 heteroaryl group; Alternatively, it may be a C2 to C40 heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a C6 to C40 aryl group and a C2 to C40 heteroaryl group.
  • R61 to R70 are hydrogen; Or deuterium; may be.
  • R71 to R74 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 It can form a heterocycle.
  • R71 to R74 are the same as or different from each other, and each independently, hydrogen; Or deuterium; Or, two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.
  • R71 to R74 are the same as or different from each other, and each independently, hydrogen; Or deuterium; Or, two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.
  • R71 to R74 are the same as or different from each other, and each independently, hydrogen; Or deuterium; Or, two or more groups adjacent to each other may be bonded to each other to form a C6 to C60 aromatic hydrocarbon ring.
  • R71 to R74 are the same as or different from each other, and each independently, hydrogen; Or deuterium; Or, two or more groups adjacent to each other may be bonded to each other to form a C6 to C40 aromatic hydrocarbon ring.
  • R71 to R74 are the same as or different from each other, and each independently, hydrogen; Or deuterium; Or, two or more groups adjacent to each other may be bonded to each other to form a benzene ring.
  • Rd and Re are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; Or it may be a substituted or unsubstituted C6 to C60 aryl group.
  • Rd and Re may be the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C60 alkyl group.
  • Rd and Re may be the same as or different from each other, and each independently may be a C1 to C40 alkyl group.
  • Rd and Re may be a methyl group.
  • R81 and R82 are the same as or different from each other, and each independently, a substituted or unsubstituted C10 or more aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R81 and R82 are the same as or different from each other, and each independently, a substituted or unsubstituted C10 or more and C60 or less aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R81 and R82 are the same as or different from each other, and each independently, a substituted or unsubstituted C10 or more and C40 or less aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.
  • R81 and R82 are the same as or different from each other, and each independently, a C10 or more and C40 or less aryl group unsubstituted or substituted with a C1 to C20 alkyl group; Or it may be a C2 to C40 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group.
  • R81 and R82 may be represented by the following Chemical Formula 13.
  • A2 is NR96; O; S; Or CR97R98,
  • R91 to R95 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle And
  • R96 to R98 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
  • k is an integer from 0 to 3.
  • R83 is a substituted or unsubstituted aryl group of less than C10.
  • R83 is an aryl group of less than C10 unsubstituted or substituted with a C6 to C10 aryl group or a C2 to C20 heteroaryl group.
  • R83 is a phenyl group unsubstituted or substituted with a phenyl group or a dibenzofuran group; Biphenyl group; Or it may be a naphthyl group.
  • R91 to R95 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C60 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.
  • R91 to R95 are the same as or different from each other, and each independently hydrogen; Or deuterium; Or, two or more groups adjacent to each other may be bonded to each other to form a benzene ring.
  • R96 to R98 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R96 to R98 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1 to C20 alkyl group; It may be a C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1 to C20 alkyl group, a C6 to C40 aryl group, and a C2 to C40 heteroaryl group.
  • the heterocyclic compound represented by Formula 2 may be any one of the following compounds.
  • Formula 2 may be included in an emission layer among the organic material layers.
  • Formula 2 may be included in an emission layer among the organic material layers, and specifically, may be used as a host material for the emission layer.
  • the host material of the emission layer of the organic light emitting device may include the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 at the same time.
  • a composition for an organic material layer of an organic light-emitting device including a heterocyclic compound represented by Formula 1 and a compound represented by Formula 2 is provided.
  • the heterocyclic compound represented by Formula 1 in the composition the weight ratio of the heterocyclic compound represented by Formula 2 may be 1: 10 to 10: 1, 1: 8 to 8: 1, and 1: 5 To 5: 1, may be 1: 2 to 2: 1, but is not limited thereto.
  • the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 are pre-mixed to form using a thermal vacuum deposition method. It provides a method of manufacturing an organic light emitting device.
  • the pre-mixed means that the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are first mixed and mixed in a park before depositing the compound represented by Chemical Formula 1 on the organic material layer.
  • the premixed material may be referred to as a composition for an organic material layer according to an exemplary embodiment of the present application.
  • the cathode material Materials having a relatively large work function may be used as the cathode material, and transparent conductive oxide, metal, or conductive polymer may be used.
  • the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material Materials having a relatively low work function may be used as the cathode material, and metal, metal oxide, or conductive polymer may be used.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • a known hole injection material may be used.
  • a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a phthalocyanine compound disclosed in Advanced Material, 6, p.677 (1994) is described.
  • Starburst type amine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/camphor sulfonic acid or polyaniline/ Poly(4-styrene-sulfonate) (Polyaniline/Poly(4-styrene-sulfonate)), etc. may be used.
  • TCTA
  • hole transport material pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular weight or high molecular weight materials may be used.
  • Electron transport materials include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used, and not only low-molecular substances but also high-molecular substances may be used.
  • LiF is typically used in the art, but the present application is not limited thereto.
  • Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited as separate sources and used, or premixed and deposited as one source. Further, a fluorescent material may be used as the light emitting material, but it may also be used as a phosphorescent material. As the light-emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used alone, but materials in which a host material and a dopant material are both involved in light emission may be used.
  • hosts of the same series may be mixed and used, or hosts of different types may be mixed and used.
  • any two or more types of an n-type host material or a p-type host material may be selected and used as the host material of the light emitting layer.
  • the organic light-emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the heterocyclic compound according to the exemplary embodiment of the present application may function in an organic electronic device including an organic solar cell, an organic photoreceptor, an organic transistor, etc. with a principle similar to that applied to an organic light emitting device.
  • 155 ⁇ 8.55(d, 1H), 8.28(d, 1H), 8.11 ⁇ 8.09(d, 2H), 7.96 ⁇ 7.89(m, 5H), 7.78 ⁇ 7.69(m, 3H), 7.55 ⁇ 7.50(m, 7H) ), 7.40-7.28 (m, 6H), 7.16 (t, 1H).
  • 157 ⁇ 8.95(d, 1H), 8.55(d, 2H), 8.36 ⁇ 8.28(d, 3H), 8.11 ⁇ 8.09(m, 2H), 7.98 ⁇ 7.94(m, 5H), 7.77 ⁇ 7.69(m, 3H) ), 7.55 ⁇ 7.50(m, 7H), 7.40 ⁇ 7.31(m, 7H), 7.16(t, 1H).
  • 158 ⁇ 8.55(d, 1H), 8.36(d, 2H), 8.18(s, 1H), 8.11(d, 1H), 7.98 ⁇ 7.90(m, 4H), 7.75 ⁇ 7.68(m, 4H), 7.55 ⁇ 7.50(m, 7H), 7.40 ⁇ 7.28(m, 6H), 7.16(t, 1H).
  • 160 ⁇ 8.55(d, 1H), 8.28(d, 1H), 8.11 ⁇ 8.08(d, 2H), 7.96 ⁇ 7.88(m, 7H), 7.75 ⁇ 7.69(m, 4H), 7.55 ⁇ 7.25(m, 16H) ), 7.16 (t, 1H).
  • 161 ⁇ 9.09(s, 1H), 8.55(d, 2H),8.28(d, 1H), 8.16 ⁇ 7.94(m, 9H), 7.75 ⁇ 7.16(m, 19H)
  • 162 ⁇ 8.55 (d, 1H), 8.28 (d, 1H), 8.11-7.94 (m, 11H), 7.75-7.30 (m, 22H), 7.16 (t, 1H).
  • 163 ⁇ 8.55(d, 1H), 8.28(d, 1H), 8.11(d, 1H), 8.03 ⁇ 7.94(m, 7H), 7.82 ⁇ 7.69(m, 6H), 7.55 ⁇ 7.25(m, 15H), 7.16 (t, 1H).
  • 169 ⁇ 8.54(d, 2H), 8.01(d, 2H), 7.91(s, 1H), 7.79 ⁇ 7.70(m, 9H), 7.65 ⁇ 7.60(m, 10H), 7.51 ⁇ 7.45(m, 6H), 7.18 (d, 1H).
  • 170 ⁇ 8.55(d, 1H), 8.28(d, 1H), 8.11(d, 1H), 7.98 ⁇ 7.90(m, 7H), 7.78 ⁇ 7.69(m, 5H), 7.55 ⁇ 7.25(m, 15H), 7.16 (t, 1H).
  • 172 ⁇ 8.55 (d, 2H), 8.36 (d, 2H), 8.06 to 7.94 (m, 9H), 7.63 to 7.50 (m, 12H), 7.39 to 7.25 (m, 6H), 7.16 (t, 1H).
  • 175 ⁇ 8.55 (d, 2H), 8.36(d, 2H), 8.09(d, 1H), 7.99 ⁇ 7.89(m, 6H), 7.78(d, 1H), 7.65 ⁇ 7.50(m, 10H), 7.39 ⁇ 7.28 (m, 5H), 7.16 (t, 1H).
  • a glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as acetone, methanol, and isopropyl alcohol, dried, and UVO treated for 5 minutes using UV in a UV scrubber. After the substrate was transferred to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tin oxide
  • the hole injection layer 2-TNATA (4,4'4"-Tris[2-naphthyl(phenyl)amino] triphenylamine) and the hole transport layer NPB (N,N'-diphenyl-() are a common layer on the ITO transparent electrode (anode) 1,1'-biphenyl)-4,4'-diamine) was formed.
  • the light emitting layer was thermally vacuum deposited thereon as follows.
  • the light emitting layer was doped with (piq) 2 (Ir) (acac) in a 3% weight ratio to the host using the compound shown in Table 8 below as a host, red phosphorescent dopant (piq) 2 (Ir) (acac), and deposited 500 ⁇ . .
  • piq red phosphorescent dopant
  • acac red phosphorescent dopant
  • 60 ⁇ of BCP was deposited as a hole blocking layer
  • 200 ⁇ of Alq 3 was deposited as an electron transport layer thereon.
  • lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 ⁇ to form a cathode.
  • An electroluminescent device was manufactured.
  • Table 8 below is an example of applying a single host material
  • Table 9 shows that the first host is a compound (acceptor (n-Host)) corresponding to the present formula 1 having good electron transport ability, and the second host has good hole transport ability.
  • This is an example in which two host compounds are deposited as one source using a compound (donor (p-Host)) corresponding to Formula 2 of the present application.
  • Table 9 shows that when the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are simultaneously included in the organic material layer of the organic light emitting device, it can be seen that driving voltage, efficiency, and lifetime can be improved. This result can be expected to cause an exciplex phenomenon, including both compounds at the same time.
  • the exciplex phenomenon refers to the formation of a dicomplex in an excited state through electron exchange between molecules having strong donor properties and molecules having strong acceptor properties.
  • FIG. 4 is a diagram illustrating an exciplex phenomenon. As shown in FIG. 4, when an exciplex phenomenon occurs, a new S1 energy level and a T1 energy level are formed, and a change in PL red-shifted from each molecule can be confirmed.
  • FIG. 5 is a photoluminescence (PL) measurement data of only a first host and a second host according to Example 71 of the present application
  • FIG. 6 includes a first host and a second host according to Example 71 of the present application. This is the PL (photoluminescence) measurement data.
  • PL photoluminescence
  • RISC Reverse Intersysterm Crossing
  • the compound of Formula 1 in the case of the compound of Formula 1, it does not have a strong acceptor ability as a bipolar compound, but exciplex shows a red shifted PL change by injecting donor (p-Host), a compound of Formula 2 with good hole transport ability. (ecxiplex) can be formed, thereby helping to improve light-emitting characteristics.
  • donor p-Host
  • ecxiplex can be formed, thereby helping to improve light-emitting characteristics.
  • the compound (donor (p-host)) corresponding to Formula 2 of the present invention having good hole transport ability was injected, it was confirmed that the lifespan was significantly improved by appropriate movement of the light emitting zone in the light emitting layer.
  • a glass substrate coated with a thin film of indium tinoxide (ITO) to a thickness of 1,500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV in a UV (Ultraviolet) scrubber. Thereafter, the substrate was transferred to a plasma cleaner (PT), followed by plasma treatment to remove the ITO work function and residual film in a vacuum state, and transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tinoxide
  • the light emitting layer was thermally vacuum deposited as follows. Specifically, each of the compounds described in Examples 1 to 26 of Table 10 was used as the red host of the emission layer, and the red phosphorescent dopant (piq) 2 (Ir) (acac) was doped with 3wt% to the red host A light emitting layer of 500 ⁇ was deposited. Then, 60 ⁇ of Bathocuproine (hereinafter, BCP) was deposited as a hole blocking layer, and 200 ⁇ of Alq 3 was deposited as an electron transport layer thereon.
  • BCP Bathocuproine
  • lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 ⁇ to form a cathode.
  • Al aluminum
  • Electroluminescence (EL) characteristics were measured with McScience's M7000 for the organic light emitting devices of Examples 1 to 26 manufactured as described above, and the life equipment measuring equipment (M6000) manufactured by McScience was used with the measurement results.
  • M6000 life equipment measuring equipment
  • T 90 was measured.
  • the T 90 refers to a lifetime (unit: h, hour) that is 90% of the initial luminance.
  • the measured characteristics of the organic light emitting device are shown in Table 10 below.
  • Example 1 301 2.54 3.43 48.2 (0.680, 0.320) 190
  • Example 2 304 2.68 3.48 47.1 (0.676, 0.323) 185
  • Example 3 307 2.49 3.47 48.7 (0.681, 0.319) 197
  • Example 4 309 2.51 3.57 49.7 (0.678, 0.321) 192
  • Example 5 319 2.66 3.61 43.2 (0.676, 0.323) 175
  • Example 6 323 2.50 3.55 44.7 (0.683, 0.316) 178
  • Example 7 333 2.49 3.57 43.6 (0.680, 0.319) 168
  • Example 8 335 2.53 3.51 44.7 (0.680, 0.320) 171
  • Example 9 340 2.47 3.62 43.2 (0.678, 0.321) 181
  • Example 10 342 2.44 3.57 44.1 (0.680, 0.319) 175
  • Example 11 346 2.53 3.55 41.1 (0.679, 0.320)
  • a glass substrate coated with a thin film of indium tinoxide (ITO) to a thickness of 1,500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV in a UV (Ultraviolet) scrubber. Thereafter, the substrate was transferred to a plasma cleaner (PT), followed by plasma treatment to remove the ITO work function and residual film in a vacuum state, and transferred to a thermal evaporation equipment for organic deposition.
  • ITO indium tinoxide
  • the light emitting layer was thermally vacuum deposited as follows. Specifically, the compounds described in Examples 1 to 26 of Table 11 were used as the red host of the emission layer, and a red phosphorescent dopant (piq) 2 (Ir) (acac) was doped with 3 wt% to the red host to have a thickness of 500 ⁇ . The emissive layer was deposited. Then, 60 ⁇ of Bathocuproine (hereinafter, BCP) was deposited as a hole blocking layer, and 200 ⁇ of Alq3 was deposited as an electron transport layer thereon.
  • BCP Bathocuproine
  • lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 ⁇ to form a cathode.
  • Al aluminum
  • T 90 refers to a lifetime (unit: h, hour) that is 90% of the initial luminance.
  • the measured characteristics of the organic light-emitting device are shown in Table 11 below.
  • Table 11 is a case in which the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are simultaneously included in the organic material layer of the organic light-emitting device. You can expect it to happen.
  • the heterigori compound of Formula 2 serves as an Electron blocking layer (EBL) based on a high LUMO level, thereby helping excited electrons to stay in the emission layer area, thereby creating an effective emission area.
  • EBL Electron blocking layer

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  • Spectroscopy & Molecular Physics (AREA)
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  • Electroluminescent Light Sources (AREA)
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Abstract

La présente invention concerne un composé hétérocyclique représenté par la formule chimique 1, un dispositif électroluminescent organique le comprenant, une composition pour une couche organique d'un dispositif électroluminescent organique, et un procédé de fabrication d'un dispositif électroluminescent organique.
PCT/KR2020/016200 2019-11-21 2020-11-17 Composé hétérocyclique, dispositif électroluminescent organique le comprenant, composition pour couche organique de dispositif électroluminescent organique, et procédé de fabrication de dispositif électroluminescent organique WO2021101220A1 (fr)

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JP2021571737A JP2023500759A (ja) 2019-11-21 2020-11-17 ヘテロ環化合物、これを含む有機発光素子、有機発光素子の有機物層用組成物および有機発光素子の製造方法
CN202080048175.3A CN114096535A (zh) 2019-11-21 2020-11-17 杂环化合物、包括其的有机发光元件、用于有机发光元件的有机层的组成物及有机发光元件制造方法
US17/612,956 US20220259187A1 (en) 2019-11-21 2020-11-17 Heterocyclic compound, organic light emitting device comprising same, composition for organic layer of organic light emitting device, and method for manufacturing organic light emitting device
EP20889890.8A EP4063359A4 (fr) 2019-11-21 2020-11-17 Composé hétérocyclique, dispositif électroluminescent organique le comprenant, composition pour couche organique de dispositif électroluminescent organique, et procédé de fabrication de dispositif électroluminescent organique

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TWI795694B (zh) 2023-03-11

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